EP0043924A1 - Process for the continuous extraction of caprolactam from aqueous solutions containing aprolactam and its oligomers - Google Patents
Process for the continuous extraction of caprolactam from aqueous solutions containing aprolactam and its oligomers Download PDFInfo
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- EP0043924A1 EP0043924A1 EP81104595A EP81104595A EP0043924A1 EP 0043924 A1 EP0043924 A1 EP 0043924A1 EP 81104595 A EP81104595 A EP 81104595A EP 81104595 A EP81104595 A EP 81104595A EP 0043924 A1 EP0043924 A1 EP 0043924A1
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- EP
- European Patent Office
- Prior art keywords
- caprolactam
- extraction
- oligomers
- aqueous solutions
- organic solvents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/16—Separation or purification
Definitions
- This object is achieved in a process for the continuous extraction of caprolactam from such and its aqueous solutions containing oligomers with organic solvents, a caprolactam and aqueous solution containing its oligomers being added in the upper part of an extraction zone and organic solvents in the lower part, at the upper end removes a solution of caprolactam in the organic solvent and in the lower end an aqueous phase containing oligomers, characterized in that liquid aromatic hydrocarbons are used and the extraction is carried out at a pH of 2.0 to 6.0.
- the new method has the advantage that the extraction proceeds smoothly and there are no disturbances caused by the oligomers.
- the aqueous solutions to be extracted generally contain 2 to 20% by weight of caprolactam and, based on the organic compounds contained in the aqueous solution, 15 to 25% by weight of oligomers of caprolactam. Particularly preferred solutions contain 3 to 10% by weight of caprolactam and the corresponding amounts of oligomers.
- Such solutions can be obtained e.g. by extraction of polycaprolactam with water, as described for example in DE-PS 22 42 641.
- aqueous solutions containing caprolactam of other origin can also be used in the extraction, e.g. aqueous solutions that are obtained during the extraction of crude lactam.
- liquid aromatic hydrocarbons such as benzene, xylene or toluene.
- Preferred aromatic hydrocarbons are benzene or toluene. It is advantageous to use 2 to 12 times, in particular 2.5 to 10 times, each part by weight of aqueous solution
- the extraction is preferably carried out at a temperature of 30 to 70 ° C and under atmospheric pressure or slightly elevated pressure e.g. up to 1.5 bar through.
- the extraction is carried out at a pH of 2.0 to 6.0, in particular 2.5 to 5.0.
- caprolactam and its wash water containing oligomers are used alone, it is expedient to acidify them before the extraction with non-oxidizing mineral acids, such as sulfuric acid or phosphoric acid, in particular sulfuric acid, up to the above-mentioned pH.
- non-oxidizing mineral acids such as sulfuric acid or phosphoric acid, in particular sulfuric acid, up to the above-mentioned pH.
- Aqueous solutions containing caprolactam are also used which, for the extraction of crude lactam, contain e.g. acc. to DE-PS 11,994,863, also used, so there is no need to acidify, since these aqueous solutions already have the desired pH.
- the procedure advantageously is such that in the extraction zone the aqueous solution containing caprolactam and its oligomers is added in the upper fifth and liquid aromatic hydrocarbon in the lower fifth, a solution of caprolactam in liquid aromatic hydrocarbons at the upper end of the column and an oligomer of Aqueous phase containing caprolactams is removed.
- the extraction in conventional extraction columns, e.g. Sieve tray columns, packed columns, pulsed packing or stirring disk columns carried out. Suitable columns have, for example, 10 to 50 trays.
- caprolactam in liquid aromatic hydrocarbons obtained which contains, for example, 0.5 to 8% by weight of caprolactam, is advantageously used as an extractant in the extraction of crude lactam, as described in DE-PS 26 56 182.
- the oligomers of caprolactam can be separated off and worked up, for example by thermal cleavage, to form monomeric caprolactam.
- caprolactam In the production of caprolactam by Beckmann's rearrangement, a crude lactam is obtained which is purified by extraction with benzene. The resulting benzene lactam phase is worked up to caprolactam. A brown solution is obtained as the aqueous phase, which contains ammonium sulfate, impurities and a little caprolactam.
- 10 t of this brown aqueous phase with a lactam content of 1.0% by weight and a pH of 4.2 are fed hourly to the top of 25 trays of a sieve tray column with a diameter of 2,500 mm. 50,549 kg / h of benzene are fed to the bottom floor every hour.
- the temperature in the extraction column is 60 to 65 ° C.
- 10 m 3 of an extraction water from the polyamide production with 4% caprolactam and 0.8% oligomers with a pH of 5.1 and a temperature of 60 to 65 ° C per hour are also fed to the top floor.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyamides (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
Verfahren zur kontinuierlichen Extraktion von Caprolactam aus solches und dessen Oligomere enthaltenden wäßrigen Lösungen mit organischen Lösungsmitteln, wobei man im oberen Teil einer Extraktionszone eine Caprolactam und dessen Oligomere enthaltende wäßrige Lösung und im unteren Teil organische Lösungsmittel zuführt, am oberen Ende eine Lösung von Caprolactam in organischen Lösungsmitteln und am unteren Ende eine Oligomere des Caprolactams enthaltende wäßrige Phase abführt, wobei man flüssige aromatische Kohlenwasserstoffe verwendet und die Extraktion bei einem pH-Wert von 2,0 bis 6,0 durchführt.A process for the continuous extraction of caprolactam from such and its aqueous solutions containing oligomers with organic solvents, wherein in the upper part of an extraction zone a caprolactam and its aqueous solution containing oligomers are added and in the lower part organic solvents, at the upper end a solution of caprolactam in organic Solvents and at the bottom of an aqueous phase containing oligomers of caprolactam, using liquid aromatic hydrocarbons and performing the extraction at a pH of 2.0 to 6.0.
Description
Bei der Extraktion von Polycaprolactam mit Wasser zur Ent- .fernung von Monomeren erhält man wäßrige Lösungen, die Caprolactam und dessen Oligomere enthalten. Es ist erforderlich, monomeres Caprolactam aus solches enthaltenden Lösungen wiederzugewinnen.The extraction of polycaprolactam with water to remove monomers gives aqueous solutions which contain caprolactam and its oligomers. It is necessary to recover monomeric caprolactam from such containing solutions.
Aus der DL-PS 9 215 ist bekannt, Caprolactam enthaltende Waschwässer zunächst teilweise einzuengen, dabei ausgefallene Oligomere durch Filtration zu entfernen, das Filtrat mit Lösungsmitteln zu extrahieren und aus der Lösungsmittelphase das Caprolactam zu isolieren. Eine solche Arbeitsweise ist jedoch energetisch aufwendig und außerdem bereitet die Filtration des ausgefallenen Oligomeren Schwierigkeiten. Entsprechend der DE-OS 17 70 088 führt man die Extraktion von Caprolactam enthaltenden Waschwässern mit einem mit Wasser nicht mischbaren Lösungsmittel durch, wobei das Lösungsmittel einen Verteilungskoeffizienten bei 25°C für Caprolactam im System Lösungsmittel/Wasser von mindestens 0,2 hat und eine kleinere Dichte als die wäßrige Phase oder eine größere Dichte als die der oligomeren Feststoffe aufweist. Bei der technischen Verwirklichung eines solchen Verfahrens im kontinuierlichen Betrieb treten jedoch immer wieder Schwierigkeiten durch oligomere Feststoffe auf, insbesondere treten Verstopfungen der Extraktionskolonnen ein.From DL-PS 9 215 it is known to first partially narrow down washing water containing caprolactam, to remove precipitated oligomers by filtration, to extract the filtrate with solvents and to isolate the caprolactam from the solvent phase. However, such a procedure is energy-intensive and, in addition, the filtration of the precipitated oligomer is difficult. According to DE-OS 17 70 088, the extraction of wash water containing caprolactam is carried out with a water-immiscible solvent, the solvent having a distribution coefficient at 25 ° C. for caprolactam in the solvent / water system of at least 0.2 and a smaller one Has density than the aqueous phase or a density greater than that of the oligomeric solids. In the technical implementation of such a method in continuous operation, however, difficulties repeatedly arise due to oligomeric solids, in particular clogging of the extraction columns.
Es war deshalb die technische Aufgabe gestellt, die Extraktion von Caprolactam aus solches und dessen Oligomere enthaltenden wäßrigen Lösungen so zu gestalten, daß die Extraktion reibungslos verläuft und keine Störungen durch die Oligomeren auftreten.It was therefore the technical problem to design the extraction of caprolactam from such and its aqueous solutions containing oligomers so that the extraction proceeds smoothly and no interference from the oligomers occur.
Diese Aufgabe wird gelöst in einem Verfahren zur kontinuierlichen Extraktion von Caprolactam aus solches und dessen Oligomere enthaltenden wäßrigen Lösungen mit organischen Lösungsmitteln, wobei man im oberen Teil einer Extraktionszone eine Caprolactam und dessen Oligomere enthaltende wäßrige Lösung und im unteren Teil organische Lösungsmittel zuführt, am oberen Ende eine Lösung von Caprolactam im organischen Lösungsmittel und im unteren Ende eine Oligomeren enthaltende wäßrige Phase abführt, dadurch gekennzeichnet, daß man flüssige aromatische Kohlenwasserstoffe verwendet und die Extraktion bei einem pH-Wert von 2,0 bis 6,0 durchführt.This object is achieved in a process for the continuous extraction of caprolactam from such and its aqueous solutions containing oligomers with organic solvents, a caprolactam and aqueous solution containing its oligomers being added in the upper part of an extraction zone and organic solvents in the lower part, at the upper end removes a solution of caprolactam in the organic solvent and in the lower end an aqueous phase containing oligomers, characterized in that liquid aromatic hydrocarbons are used and the extraction is carried out at a pH of 2.0 to 6.0.
Das neue Verfahren hat den Vorteil, daß die Extraktion reibungslos verläuft und keine-Störungen durch die Oligomeren auftreten.The new method has the advantage that the extraction proceeds smoothly and there are no disturbances caused by the oligomers.
Die zur extrahierenden wäßrigen Lösungen enthalten in der Regel 2 bis 20 Gew.% Caprolactam und bezogen auf die in der wäßrigen Lösung enthaltenen organischen Verbindungen 15 bis 25 Gew.% Oligomere des Caprolactams. Besonders bevorzugte Lösungen enthalten 3 bis 10 Gew.% Caprolactam und die entsprechenden Mengen an Oligomeren. Solche Lösungen erhält man z.B. durch Extraktion von Polycaprolactam mit Wasser, wie sie beispielsweise in DE-PS 22 42 641 beschrieben wird. Zusätzlich können bei der Extraktion noch Caprolactam enthaltende wäßrige Lösungen anderen Ursprungs mitverwendet werden, z.B. wäßrige Lösungen, die bei der Extraktion von Rohlactam anfallen.The aqueous solutions to be extracted generally contain 2 to 20% by weight of caprolactam and, based on the organic compounds contained in the aqueous solution, 15 to 25% by weight of oligomers of caprolactam. Particularly preferred solutions contain 3 to 10% by weight of caprolactam and the corresponding amounts of oligomers. Such solutions can be obtained e.g. by extraction of polycaprolactam with water, as described for example in DE-PS 22 42 641. In addition, aqueous solutions containing caprolactam of other origin can also be used in the extraction, e.g. aqueous solutions that are obtained during the extraction of crude lactam.
Die Extraktion führt man mit flüssigen aromatischen Kohlenwasserstoffen, wie Benzol, Xylol oder Toluol durch. Bevorzugte aromatische Kohlenwasserstoffe sind Benzol oder Toluol. Vorteilhaft wendet man je Gewichtsteil wäßrige Lösung die 2- bis 12-fache, insbesondere 2,5- bis 10-facheThe extraction is carried out with liquid aromatic hydrocarbons, such as benzene, xylene or toluene. Preferred aromatic hydrocarbons are benzene or toluene. It is advantageous to use 2 to 12 times, in particular 2.5 to 10 times, each part by weight of aqueous solution
Gewichtsmenge an flüssigen aromatischen Kohlenwasserstoffen an. Die Extraktion führt man vorzugsweise bei einer Temperatur von 30 bis 70°C und unter Atmosphärendruck oder schwach erhöhtem Druck z.B. bis zu 1,.5 bar durch.Weight amount of liquid aromatic hydrocarbons. The extraction is preferably carried out at a temperature of 30 to 70 ° C and under atmospheric pressure or slightly elevated pressure e.g. up to 1.5 bar through.
Erfindungsgemäß führt man die Extraktion bei einem pH-Wert von 2,0 bis 6,0, insbesondere 2,5 bis 5,0 durch. Verwendet man Caprolactam und dessen Oligomere enthaltende Waschwässer allein, so säuert man diese zweckmäßig vor der Extraktion mit nichtoxidierenden Mineralsäuren, wie Schwefelsäure oder Phosphorsäure, insbesondere Schwefelsäure bis zu dem oben genannten pH-Wert an. Werden zusätzlich Caprolactam enthaltende wäßrige Lösungen, die bei der Extraktion von Rohlactam die z.B. nach der DE-PS 11 .94 863 anfallen, mitverwendet, so erübrigt sich ein Ansäuern, da diese wäßrigen Lösungen bereits von sich aus, den gewünschten pH-Wert aufweisen.According to the invention, the extraction is carried out at a pH of 2.0 to 6.0, in particular 2.5 to 5.0. If caprolactam and its wash water containing oligomers are used alone, it is expedient to acidify them before the extraction with non-oxidizing mineral acids, such as sulfuric acid or phosphoric acid, in particular sulfuric acid, up to the above-mentioned pH. Aqueous solutions containing caprolactam are also used which, for the extraction of crude lactam, contain e.g. acc. to DE-PS 11,994,863, also used, so there is no need to acidify, since these aqueous solutions already have the desired pH.
Man verfährt vorteilhaft so, daß man in der Extraktionszone im oberen fünftel die Caprolactam und dessen Oligomere enthaltende wäßrige Lösung und im unteren fünftel flüssige aromatische Kohlenwasserstoff zugibt, am oberen Ende der Kolonne eine Lösung von Caprolactam in flüssigen aromatischen Kohlenwasserstoffen und im unteren Ende eine Oligomeren des Caprolactams enthaltende wäßrige Phase entnimmt. Vorteilhaft wird die Extraktion in üblichen Extraktionskolonnen, z.B. Siebbodenkolonnen, Füllkörperkolonnen, pulsierten Füllkörpern oder Rührscheibenkolonnen durchgeführt. Geeignete Kolonnen haben beispielsweise 10 bis 50 Böden.The procedure advantageously is such that in the extraction zone the aqueous solution containing caprolactam and its oligomers is added in the upper fifth and liquid aromatic hydrocarbon in the lower fifth, a solution of caprolactam in liquid aromatic hydrocarbons at the upper end of the column and an oligomer of Aqueous phase containing caprolactams is removed. The extraction in conventional extraction columns, e.g. Sieve tray columns, packed columns, pulsed packing or stirring disk columns carried out. Suitable columns have, for example, 10 to 50 trays.
Die erhaltene Lösung von Caprolactam in flüssigen aromatischen Kohlenwasserstoffen, die z.B. 0,5 bis 8 Gew.% Caprolactam enthält, wird vorteilhaft als Extraktionsmittel bei der Extraktion von Rohlactam, wie sie in der DE-PS 26 56 182 beschrieben wird, verwendet. Aus der wäß- rigen Phase können die Oligomeren des Caprolactams abgetrennt werden und z.B. durch thermische Spaltung auf monomeres Caprolactam aufgearbeitet werden.The solution of caprolactam in liquid aromatic hydrocarbons obtained, which contains, for example, 0.5 to 8% by weight of caprolactam, is advantageously used as an extractant in the extraction of crude lactam, as described in DE-PS 26 56 182. From the water phase, the oligomers of caprolactam can be separated off and worked up, for example by thermal cleavage, to form monomeric caprolactam.
Das Verfahren nach der Erfindung sei an folgendem Beispiel veranschaulicht.The method according to the invention is illustrated by the following example.
Bei der Herstellung von Caprolactam durch Beckmann'sche Umlagerung fällt ein Rohlactam an, das durch Extraktion mit Benzol gereinigt wird. Die anfallende Benzol-Lactamphase wird zu Caprolactam aufgearbeitet. Als wäßrige Phase fällt eine braune Lösung an, die Ammonsulfat, Verunreinigungen und wenig Caprolactam enthält.In the production of caprolactam by Beckmann's rearrangement, a crude lactam is obtained which is purified by extraction with benzene. The resulting benzene lactam phase is worked up to caprolactam. A brown solution is obtained as the aqueous phase, which contains ammonium sulfate, impurities and a little caprolactam.
10 t dieser braunen wäßrigen Phase mit einem Lactamgehalt von 1,0 Gew.% und einem pH-Wert von 4,2 werden stündlich dem obersten von 25 Böden einer Siebbodenkolonne mit einem Durchmesser von 2.500 mm zugeführt. Dem untersten Boden werden stündlich 50.549 kg/h Benzol zugeführt. Die Temperatur in der Extraktionskolonne beträgt 60 bis 65°C. Zusätzlich werden stündlich 10 m3 eines Extraktionswassers aus der Polyamidherstellung mit 4 % Caprolactam und 0,8 % Oligomeren mit einem pH-Wert von 5,1 und einer Temperatur von 60 bis 65°C ebenfalls dem obersten Boden zugeführt.10 t of this brown aqueous phase with a lactam content of 1.0% by weight and a pH of 4.2 are fed hourly to the top of 25 trays of a sieve tray column with a diameter of 2,500 mm. 50,549 kg / h of benzene are fed to the bottom floor every hour. The temperature in the extraction column is 60 to 65 ° C. In addition, 10 m 3 of an extraction water from the polyamide production with 4% caprolactam and 0.8% oligomers with a pH of 5.1 and a temperature of 60 to 65 ° C per hour are also fed to the top floor.
Am oberen Ende der Extraktionskolonne fallen stündlich 51.111 kg/h einer Benzol-Lactam-Lösung folgender Zusammensetzung, 0,9 % Lactam, 0,2 % H20, 98,9 % Benzol, an. Diese Lösung wird zur extraktiven Reinigung des Rohlactam eingesetzt und das Benzol nach destillativer Trennung, wieder zur Extraktion der beschriebenen wäßrigen Phase verwendet.At the upper end of the extraction column, 51,111 kg / h of a benzene-lactam solution of the following composition, 0.9% lactam, 0.2% H 2 O, 98.9% benzene, are produced per hour. This solution is used for the extractive purification of the crude lactam and, after separation by distillation, the benzene is used again to extract the aqueous phase described.
Am unteren Ende der Kolonne fallen stündlich 20 t einer braunen, wäßrigen Phase an, die Ammonsulfat, Verunreinigungen, 0,2 % Caprolactam und 0,4 % Oligomere enthält. Der pH-Wert beträgt 4,6. Diese Lösung wird durch Strippen mit Dampf vom Benzol befreit welches in den Kreislauf zurückgeführt wird. Diese vom Benzol befreite Lösung kann der biologischen Behandlung zugeführt oder nach Aufkonzentration verbrannt werden. Auch nach 4-monatigem Betrieb treten keine Verstopfungsprobleme der Siebböden auf.At the lower end of the column, 20 tons of a brown, aqueous phase are obtained per hour, which contains ammonium sulfate, impurities, 0.2% caprolactam and 0.4% oligomers. The pH is 4.6. This solution is freed from the benzene by stripping with steam, which is returned to the circuit. This solution, which has been freed from benzene, can be used for biological treatment or burned after concentration. Even after 4 months of operation, there are no problems with clogging the sieve trays.
Claims (4)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3026538 | 1980-07-12 | ||
| DE19803026538 DE3026538A1 (en) | 1980-07-12 | 1980-07-12 | METHOD FOR CONTINUOUS EXTRACTION OF CAPROLACTAM AS SUCH AND AQUEOUS SOLUTIONS CONTAINING THE SAME OF THE OLIGOMER |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0043924A1 true EP0043924A1 (en) | 1982-01-20 |
| EP0043924B1 EP0043924B1 (en) | 1983-05-04 |
Family
ID=6107089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP81104595A Expired EP0043924B1 (en) | 1980-07-12 | 1981-06-15 | Process for the continuous extraction of caprolactam from aqueous solutions containing aprolactam and its oligomers |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4350630A (en) |
| EP (1) | EP0043924B1 (en) |
| JP (1) | JPS5745154A (en) |
| DE (2) | DE3026538A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0274111A2 (en) * | 1987-01-07 | 1988-07-13 | BASF Aktiengesellschaft | Method for removing benzene and toluene from exhaust gases containing the same |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19648747A1 (en) * | 1996-11-25 | 1998-05-28 | Basf Ag | Process for the recovery of caprolactam and its oligomers from aqueous polycaprolactam extracts |
| US7022844B2 (en) | 2002-09-21 | 2006-04-04 | Honeywell International Inc. | Amide-based compounds, production, recovery, purification and uses thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH417600A (en) * | 1958-10-09 | 1966-07-31 | Stamicarbon | Process for separating a lactam from an acidic reaction mixture |
| DE2656182A1 (en) * | 1976-12-11 | 1978-06-22 | Basf Ag | PROCESS FOR THE CONTINUOUS EXTRACTION OF CAPROLACTAM FROM ROHLACTAM |
| DE2724361A1 (en) * | 1977-05-28 | 1978-11-30 | Bayer Ag | CLEANING CAPROLACTAM |
| DE2550934B2 (en) * | 1975-11-13 | 1979-10-04 | Bayer Ag, 5090 Leverkusen | Purification of caprolactam |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3264060A (en) * | 1966-08-02 | Simultaneous recovery of pure ammoni- um sulfate and pure lactams from re- arrangement mixtures of alicyclic ketoximes | ||
| US2758991A (en) * | 1956-08-14 | Hvvevvtofry | ||
| DE1227469B (en) * | 1963-01-10 | 1966-10-27 | Basf Ag | Process for the preparation of omega-amino-ketocarboxylic acids |
| DE2242641C3 (en) * | 1972-08-30 | 1980-06-19 | Basf Ag, 6700 Ludwigshafen | Process for the continuous extraction of polylactams |
| NL7505130A (en) * | 1975-05-01 | 1976-11-03 | Stamicarbon | PROCEDURE FOR THE WINNING OF PURE EPSILON CAPROLACTAM FROM AN Aqueous SOLUTION OF THIS. |
-
1980
- 1980-07-12 DE DE19803026538 patent/DE3026538A1/en not_active Withdrawn
-
1981
- 1981-06-15 EP EP81104595A patent/EP0043924B1/en not_active Expired
- 1981-06-15 DE DE8181104595T patent/DE3160221D1/en not_active Expired
- 1981-06-25 US US06/276,815 patent/US4350630A/en not_active Expired - Lifetime
- 1981-06-29 JP JP56099787A patent/JPS5745154A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH417600A (en) * | 1958-10-09 | 1966-07-31 | Stamicarbon | Process for separating a lactam from an acidic reaction mixture |
| DE2550934B2 (en) * | 1975-11-13 | 1979-10-04 | Bayer Ag, 5090 Leverkusen | Purification of caprolactam |
| DE2656182A1 (en) * | 1976-12-11 | 1978-06-22 | Basf Ag | PROCESS FOR THE CONTINUOUS EXTRACTION OF CAPROLACTAM FROM ROHLACTAM |
| DE2724361A1 (en) * | 1977-05-28 | 1978-11-30 | Bayer Ag | CLEANING CAPROLACTAM |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0274111A2 (en) * | 1987-01-07 | 1988-07-13 | BASF Aktiengesellschaft | Method for removing benzene and toluene from exhaust gases containing the same |
| EP0274111A3 (en) * | 1987-01-07 | 1988-09-21 | Basf Aktiengesellschaft | Method for removing solvents which are not miscible with water from exhaust gases containing the same |
| US4804473A (en) * | 1987-01-07 | 1989-02-14 | Basf Aktiengesellschaft | Removal of water-immiscible solvents from offgases containing same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3026538A1 (en) | 1982-02-11 |
| JPS5745154A (en) | 1982-03-13 |
| US4350630A (en) | 1982-09-21 |
| EP0043924B1 (en) | 1983-05-04 |
| DE3160221D1 (en) | 1983-06-09 |
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